Acetic Acid → HCID 21498755, Verbindung

HRID 1357873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357873
C(O)(=O)C.[N+:5]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][C:9]=1[O:19][CH3:20])([O-])=O.C([O-])(O)=O.[Na+]>O>[NH2:5][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][C:9]=1[O:19][CH3:20]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 130673386-Methoxy-7-nitro-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 21498755HCID 21498755, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of acetic acid (20 mL) in H2O (100 mL), 7-nitro-6-methoxy-1-tetralone (2.21 g, 10.0 mmol) was added. The solution was heated to reflux for 1 hour, and then cooled down to rt. NaHCO3 (60 mL, saturated solution) was added, and the mixture was partitioned between CH2Cl2 and water. The organic layer was dried over anhydrous sodium sulfate. After filtration, the organic layer was concentrated in vacuo to provide a red oil. 7-Amino-6-methoxy-1-tetralone (1.74 g, 9.1 mmol, 91%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 2.07 (m, 2H), 2.57 (t, J=6.5 Hz, 2H), 2.86 (t, J=6.0 Hz, 2H), 3.73 (b, 2H), 3.91 (s, 3H), 6.59 (s, 1H), 7.36 (s, 1H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. customthe mixture was partitioned between CH2Cl2 and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe organic layer was concentrated in vacuo
  7. customto provide a red oil

Quellen und Nachweise

ORD-Eintrag
ord-d1d68466ffe2418392aa6fed27cd6cbd
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593374B2

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